For the cupcakes: Preheat the oven to 325 degrees F. Line muffin pans with paper liners.
In a medium bowl, cream together the granulated sugar, gelatin, butter and cream cheese. Beat in the eggs, one at a time, then stir in the vanilla and rum. Combine the flour and baking powder, add to the creamed mixture and mix well. Stir in the milk and strawberries until the batter is smooth. Bake for 20 to 25 minutes. The cupcakes are done when they spring back to the touch. Let cool.
For the strawberry frosting: In a medium bowl, cream together butter and cream cheese. Add the confectioners' sugar, rum and strawberry extract.
For the strawberry filling: Cut the strawberries into small pieces and place into a medium saucepan. Add the sugar and bring to a light boil. Once the filling begins to boil, turn off the heat, add the rum and let sit for 10 minutes to cool.
To assemble: Core out the center of the cupcakes and fill with strawberry filling. Then cover the tops of the cupcakes with the strawberry frosting.
This recipe was created by a contestant during a cooking competition. It has not been tested for home use.